HRP20160173T1 - Derivati 6-cikloamino-3-(1h-pirolo[2,3-b]piridin-4-il)imidazo[1,2-b]piridazina, njihova priprema i njihova terapijska primjena - Google Patents
Derivati 6-cikloamino-3-(1h-pirolo[2,3-b]piridin-4-il)imidazo[1,2-b]piridazina, njihova priprema i njihova terapijska primjena Download PDFInfo
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- HRP20160173T1 HRP20160173T1 HRP20160173T HRP20160173T HRP20160173T1 HR P20160173 T1 HRP20160173 T1 HR P20160173T1 HR P20160173 T HRP20160173 T HR P20160173T HR P20160173 T HRP20160173 T HR P20160173T HR P20160173 T1 HRP20160173 T1 HR P20160173T1
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- Croatia
- Prior art keywords
- group
- pyrrolo
- pyridin
- imidazo
- fluorophenyl
- Prior art date
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- 150000004942 imidazo[1,2-b]pyridazines Chemical class 0.000 title 1
- 230000001225 therapeutic effect Effects 0.000 title 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 28
- -1 (R)-3-methylpiperazin-1-yl Chemical group 0.000 claims 28
- 150000001875 compounds Chemical class 0.000 claims 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 10
- 125000002733 (C1-C6) fluoroalkyl group Chemical group 0.000 claims 8
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 8
- 125000004432 carbon atom Chemical group C* 0.000 claims 8
- 125000004122 cyclic group Chemical group 0.000 claims 8
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 5
- 229910052799 carbon Inorganic materials 0.000 claims 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims 4
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 229940079593 drug Drugs 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- SSJXIUAHEKJCMH-WDSKDSINSA-N (1s,2s)-cyclohexane-1,2-diamine Chemical compound N[C@H]1CCCC[C@@H]1N SSJXIUAHEKJCMH-WDSKDSINSA-N 0.000 claims 1
- BXBYNONKGASIBY-GOSISDBHSA-N (2r)-1-[4-[2-(4-fluorophenyl)-8-methyl-3-(1h-pyrrolo[2,3-b]pyridin-4-yl)imidazo[1,2-b]pyridazin-6-yl]piperazin-1-yl]propan-2-ol Chemical compound C1CN(C[C@H](O)C)CCN1C1=NN2C(C=3C=4C=CNC=4N=CC=3)=C(C=3C=CC(F)=CC=3)N=C2C(C)=C1 BXBYNONKGASIBY-GOSISDBHSA-N 0.000 claims 1
- BXBYNONKGASIBY-SFHVURJKSA-N (2s)-1-[4-[2-(4-fluorophenyl)-8-methyl-3-(1h-pyrrolo[2,3-b]pyridin-4-yl)imidazo[1,2-b]pyridazin-6-yl]piperazin-1-yl]propan-2-ol Chemical compound C1CN(C[C@@H](O)C)CCN1C1=NN2C(C=3C=4C=CNC=4N=CC=3)=C(C=3C=CC(F)=CC=3)N=C2C(C)=C1 BXBYNONKGASIBY-SFHVURJKSA-N 0.000 claims 1
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 1
- IMLQMVICBYNOHR-UHFFFAOYSA-N 1-[4-[2-(3-fluorophenyl)-8-methyl-3-(1h-pyrrolo[2,3-b]pyridin-4-yl)imidazo[1,2-b]pyridazin-6-yl]piperazin-1-yl]-2-methylpropan-2-ol Chemical compound N1=C2C(C)=CC(N3CCN(CC(C)(C)O)CC3)=NN2C(C=2C=3C=CNC=3N=CC=2)=C1C1=CC=CC(F)=C1 IMLQMVICBYNOHR-UHFFFAOYSA-N 0.000 claims 1
- FUXFHPVHJORXNM-UHFFFAOYSA-N 1-[4-[2-(4-fluorophenyl)-3-(1h-pyrrolo[2,3-b]pyridin-4-yl)imidazo[1,2-b]pyridazin-6-yl]piperazin-1-yl]-2-methylpropan-2-ol Chemical compound C1CN(CC(C)(O)C)CCN1C1=NN2C(C=3C=4C=CNC=4N=CC=3)=C(C=3C=CC(F)=CC=3)N=C2C=C1 FUXFHPVHJORXNM-UHFFFAOYSA-N 0.000 claims 1
- FXALKFFMWYBKLM-UHFFFAOYSA-N 1-[4-[2-(4-fluorophenyl)-8-methyl-3-(1h-pyrrolo[2,3-b]pyridin-4-yl)imidazo[1,2-b]pyridazin-6-yl]piperazin-1-yl]-2-methylpropan-2-ol Chemical compound N1=C2C(C)=CC(N3CCN(CC(C)(C)O)CC3)=NN2C(C=2C=3C=CNC=3N=CC=2)=C1C1=CC=C(F)C=C1 FXALKFFMWYBKLM-UHFFFAOYSA-N 0.000 claims 1
- BTKHEXSDCWTQHU-UHFFFAOYSA-N 2-(4-fluorophenyl)-6-(4-propan-2-ylpiperazin-1-yl)-3-(1h-pyrrolo[2,3-b]pyridin-4-yl)imidazo[1,2-b]pyridazine Chemical compound C1CN(C(C)C)CCN1C1=NN2C(C=3C=4C=CNC=4N=CC=3)=C(C=3C=CC(F)=CC=3)N=C2C=C1 BTKHEXSDCWTQHU-UHFFFAOYSA-N 0.000 claims 1
- RMALOSGBSYOJBF-UHFFFAOYSA-N 2-(4-fluorophenyl)-6-(4-pyrrolidin-1-ylpiperidin-1-yl)-3-(1h-pyrrolo[2,3-b]pyridin-4-yl)imidazo[1,2-b]pyridazine Chemical compound C1=CC(F)=CC=C1C1=C(C=2C=3C=CNC=3N=CC=2)N2N=C(N3CCC(CC3)N3CCCC3)C=CC2=N1 RMALOSGBSYOJBF-UHFFFAOYSA-N 0.000 claims 1
- CRQSVMCZQTWWGA-ROUUACIJSA-N 2-(4-fluorophenyl)-6-[(1s,4s)-5-methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl]-3-(1h-pyrrolo[2,3-b]pyridin-4-yl)imidazo[1,2-b]pyridazine Chemical compound C([C@]1(N(C[C@]2([H])C1)C)[H])N2C(=NN1C=2C=3C=4C=CNC=4N=CC=3)C=CC1=NC=2C1=CC=C(F)C=C1 CRQSVMCZQTWWGA-ROUUACIJSA-N 0.000 claims 1
- NPMXXTYYVZODQY-OAHLLOKOSA-N 2-(4-fluorophenyl)-6-[(3r)-3-methylpiperazin-1-yl]-3-(1h-pyrrolo[2,3-b]pyridin-4-yl)imidazo[1,2-b]pyridazine Chemical compound C1CN[C@H](C)CN1C1=NN2C(C=3C=4C=CNC=4N=CC=3)=C(C=3C=CC(F)=CC=3)N=C2C=C1 NPMXXTYYVZODQY-OAHLLOKOSA-N 0.000 claims 1
- NLRMCGCYEYFPRD-DEOSSOPVSA-N 2-(4-fluorophenyl)-6-[(3r)-3-phenylpiperazin-1-yl]-3-(1h-pyrrolo[2,3-b]pyridin-4-yl)imidazo[1,2-b]pyridazine Chemical compound C1=CC(F)=CC=C1C1=C(C=2C=3C=CNC=3N=CC=2)N2N=C(N3C[C@H](NCC3)C=3C=CC=CC=3)C=CC2=N1 NLRMCGCYEYFPRD-DEOSSOPVSA-N 0.000 claims 1
- NLRMCGCYEYFPRD-XMMPIXPASA-N 2-(4-fluorophenyl)-6-[(3s)-3-phenylpiperazin-1-yl]-3-(1h-pyrrolo[2,3-b]pyridin-4-yl)imidazo[1,2-b]pyridazine Chemical compound C1=CC(F)=CC=C1C1=C(C=2C=3C=CNC=3N=CC=2)N2N=C(N3C[C@@H](NCC3)C=3C=CC=CC=3)C=CC2=N1 NLRMCGCYEYFPRD-XMMPIXPASA-N 0.000 claims 1
- ZILKXHJSZAQZCL-UHFFFAOYSA-N 2-(4-fluorophenyl)-8-methyl-6-(3-phenylpiperazin-1-yl)-3-(1h-pyrrolo[2,3-b]pyridin-4-yl)imidazo[1,2-b]pyridazine Chemical compound N1=C2C(C)=CC(N3CC(NCC3)C=3C=CC=CC=3)=NN2C(C=2C=3C=CNC=3N=CC=2)=C1C1=CC=C(F)C=C1 ZILKXHJSZAQZCL-UHFFFAOYSA-N 0.000 claims 1
- JLQZLTYGNOGYSU-UHFFFAOYSA-N 2-(4-fluorophenyl)-8-methyl-6-(4-propan-2-ylpiperazin-1-yl)-3-(1h-pyrrolo[2,3-b]pyridin-4-yl)imidazo[1,2-b]pyridazine Chemical compound C1CN(C(C)C)CCN1C1=NN2C(C=3C=4C=CNC=4N=CC=3)=C(C=3C=CC(F)=CC=3)N=C2C(C)=C1 JLQZLTYGNOGYSU-UHFFFAOYSA-N 0.000 claims 1
- GPMKDPGWRFCWDT-KDURUIRLSA-N 2-[(3ar,6as)-5-[2-(4-fluorophenyl)-3-(1h-pyrrolo[2,3-b]pyridin-4-yl)imidazo[1,2-b]pyridazin-6-yl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrol-2-yl]ethanol Chemical compound C([C@@H]1CN(C[C@@H]1C1)CCO)N1C(=NN1C=2C=3C=4C=CNC=4N=CC=3)C=CC1=NC=2C1=CC=C(F)C=C1 GPMKDPGWRFCWDT-KDURUIRLSA-N 0.000 claims 1
- WAXUGCHKDUYNAA-BGYRXZFFSA-N 2-[(3as,6ar)-5-[2-(4-fluorophenyl)-8-methyl-3-(1h-pyrrolo[2,3-b]pyridin-4-yl)imidazo[1,2-b]pyridazin-6-yl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrol-2-yl]ethanol Chemical compound N1=C2C(C)=CC(N3C[C@H]4CN(CCO)C[C@H]4C3)=NN2C(C=2C=3C=CNC=3N=CC=2)=C1C1=CC=C(F)C=C1 WAXUGCHKDUYNAA-BGYRXZFFSA-N 0.000 claims 1
- RHTLIQYEQKYROX-UHFFFAOYSA-N 2-[4-[2-(3-fluorophenyl)-8-methyl-3-(1h-pyrrolo[2,3-b]pyridin-4-yl)imidazo[1,2-b]pyridazin-6-yl]piperazin-1-yl]ethanol Chemical compound N1=C2C(C)=CC(N3CCN(CCO)CC3)=NN2C(C=2C=3C=CNC=3N=CC=2)=C1C1=CC=CC(F)=C1 RHTLIQYEQKYROX-UHFFFAOYSA-N 0.000 claims 1
- ZITFRYZCYILMGL-UHFFFAOYSA-N 2-[4-[2-(4-fluorophenyl)-3-(1h-pyrrolo[2,3-b]pyridin-4-yl)imidazo[1,2-b]pyridazin-6-yl]piperazin-1-yl]-2-methylpropan-1-ol Chemical compound C1CN(C(C)(CO)C)CCN1C1=NN2C(C=3C=4C=CNC=4N=CC=3)=C(C=3C=CC(F)=CC=3)N=C2C=C1 ZITFRYZCYILMGL-UHFFFAOYSA-N 0.000 claims 1
- XUTAVHVOSAPLQT-UHFFFAOYSA-N 2-[4-[2-(4-fluorophenyl)-8-methyl-3-(1h-pyrrolo[2,3-b]pyridin-4-yl)imidazo[1,2-b]pyridazin-6-yl]piperazin-1-yl]ethanol Chemical compound N1=C2C(C)=CC(N3CCN(CCO)CC3)=NN2C(C=2C=3C=CNC=3N=CC=2)=C1C1=CC=C(F)C=C1 XUTAVHVOSAPLQT-UHFFFAOYSA-N 0.000 claims 1
- YJKVGNVKSOSZCB-UHFFFAOYSA-N 2-methyl-6-(4-propan-2-ylpiperazin-1-yl)-3-(1h-pyrrolo[2,3-b]pyridin-4-yl)imidazo[1,2-b]pyridazine Chemical compound C1CN(C(C)C)CCN1C1=NN2C(C=3C=4C=CNC=4N=CC=3)=C(C)N=C2C=C1 YJKVGNVKSOSZCB-UHFFFAOYSA-N 0.000 claims 1
- YVLQOKHCHICZSH-GFCCVEGCSA-N 2-methyl-6-[(3r)-3-methylpiperazin-1-yl]-3-(1h-pyrrolo[2,3-b]pyridin-4-yl)imidazo[1,2-b]pyridazine Chemical compound C1CN[C@H](C)CN1C1=NN2C(C=3C=4C=CNC=4N=CC=3)=C(C)N=C2C=C1 YVLQOKHCHICZSH-GFCCVEGCSA-N 0.000 claims 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 1
- KAZIMGMHOIHVRG-UHFFFAOYSA-N 4-[4-[2-(4-fluorophenyl)-3-(1h-pyrrolo[2,3-b]pyridin-4-yl)imidazo[1,2-b]pyridazin-6-yl]piperazin-1-yl]-2-methylbutan-2-ol Chemical compound C1CN(CCC(C)(O)C)CCN1C1=NN2C(C=3C=4C=CNC=4N=CC=3)=C(C=3C=CC(F)=CC=3)N=C2C=C1 KAZIMGMHOIHVRG-UHFFFAOYSA-N 0.000 claims 1
- ZFPOOCQUCASBEW-UHFFFAOYSA-N 6-(3,3-dimethylpiperazin-1-yl)-2-(3-fluorophenyl)-8-methyl-3-(1h-pyrrolo[2,3-b]pyridin-4-yl)imidazo[1,2-b]pyridazine Chemical compound N1=C2C(C)=CC(N3CC(C)(C)NCC3)=NN2C(C=2C=3C=CNC=3N=CC=2)=C1C1=CC=CC(F)=C1 ZFPOOCQUCASBEW-UHFFFAOYSA-N 0.000 claims 1
- LRPTXHBQULVSHV-UHFFFAOYSA-N 6-(3,3-dimethylpiperazin-1-yl)-2-(4-fluorophenyl)-3-(1h-pyrrolo[2,3-b]pyridin-4-yl)imidazo[1,2-b]pyridazine Chemical compound C1CNC(C)(C)CN1C1=NN2C(C=3C=4C=CNC=4N=CC=3)=C(C=3C=CC(F)=CC=3)N=C2C=C1 LRPTXHBQULVSHV-UHFFFAOYSA-N 0.000 claims 1
- QHNJTKYELGCRNZ-UHFFFAOYSA-N 6-(3,3-dimethylpiperazin-1-yl)-2-(4-fluorophenyl)-8-methyl-3-(1h-pyrrolo[2,3-b]pyridin-4-yl)imidazo[1,2-b]pyridazine Chemical compound N1=C2C(C)=CC(N3CC(C)(C)NCC3)=NN2C(C=2C=3C=CNC=3N=CC=2)=C1C1=CC=C(F)C=C1 QHNJTKYELGCRNZ-UHFFFAOYSA-N 0.000 claims 1
- BNZWWNUCRDKOSK-UHFFFAOYSA-N 6-(3,3-dimethylpiperazin-1-yl)-2-methyl-3-(1h-pyrrolo[2,3-b]pyridin-4-yl)imidazo[1,2-b]pyridazine Chemical compound N=1N2C(C=3C=4C=CNC=4N=CC=3)=C(C)N=C2C=CC=1N1CCNC(C)(C)C1 BNZWWNUCRDKOSK-UHFFFAOYSA-N 0.000 claims 1
- RUIQTGAVOHTSFH-UHFFFAOYSA-N 6-(4-benzylpiperazin-1-yl)-2-(4-fluorophenyl)-3-(1h-pyrrolo[2,3-b]pyridin-4-yl)imidazo[1,2-b]pyridazine Chemical compound C1=CC(F)=CC=C1C1=C(C=2C=3C=CNC=3N=CC=2)N2N=C(N3CCN(CC=4C=CC=CC=4)CC3)C=CC2=N1 RUIQTGAVOHTSFH-UHFFFAOYSA-N 0.000 claims 1
- ROKFMSLQEPTUAH-HDICACEKSA-N 6-[(3ar,6as)-2-methyl-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrol-5-yl]-2-(4-fluorophenyl)-3-(1h-pyrrolo[2,3-b]pyridin-4-yl)imidazo[1,2-b]pyridazine Chemical compound C([C@@H]1CN(C[C@@H]1C1)C)N1C(=NN1C=2C=3C=4C=CNC=4N=CC=3)C=CC1=NC=2C1=CC=C(F)C=C1 ROKFMSLQEPTUAH-HDICACEKSA-N 0.000 claims 1
- IVBSHHRBBVBURL-KDURUIRLSA-N 6-[(3ar,6as)-2-methyl-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrol-5-yl]-2-(4-fluorophenyl)-8-methyl-3-(1h-pyrrolo[2,3-b]pyridin-4-yl)imidazo[1,2-b]pyridazine Chemical compound C([C@@H]1CN(C[C@@H]1C1)C)N1C(=NN1C=2C=3C=4C=CNC=4N=CC=3)C=C(C)C1=NC=2C1=CC=C(F)C=C1 IVBSHHRBBVBURL-KDURUIRLSA-N 0.000 claims 1
- RFCWSBAITONBJH-GASCZTMLSA-N 6-[(3ar,6as)-2-methyl-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrol-5-yl]-2-methyl-3-(1h-pyrrolo[2,3-b]pyridin-4-yl)imidazo[1,2-b]pyridazine Chemical compound C([C@@H]1CN(C[C@@H]1C1)C)N1C(=NN12)C=CC1=NC(C)=C2C1=CC=NC2=C1C=CN2 RFCWSBAITONBJH-GASCZTMLSA-N 0.000 claims 1
- FPTYGFVUKUUSDF-BETUJISGSA-N 6-[(3r,5s)-3,5-dimethylpiperazin-1-yl]-2-methyl-3-(1h-pyrrolo[2,3-b]pyridin-4-yl)imidazo[1,2-b]pyridazine Chemical compound C1[C@@H](C)N[C@@H](C)CN1C1=NN2C(C=3C=4C=CNC=4N=CC=3)=C(C)N=C2C=C1 FPTYGFVUKUUSDF-BETUJISGSA-N 0.000 claims 1
- MRLIMDQKNPCDNU-IYBDPMFKSA-N 6-[(3s,5r)-3,5-dimethylpiperazin-1-yl]-2-(4-fluorophenyl)-3-(1h-pyrrolo[2,3-b]pyridin-4-yl)imidazo[1,2-b]pyridazine Chemical compound C1[C@@H](C)N[C@@H](C)CN1C1=NN2C(C=3C=4C=CNC=4N=CC=3)=C(C=3C=CC(F)=CC=3)N=C2C=C1 MRLIMDQKNPCDNU-IYBDPMFKSA-N 0.000 claims 1
- XWNMOLQVBLTAJA-XXBNENTESA-N 6-[(4ar,7ar)-1-methyl-3,4,4a,5,7,7a-hexahydro-2h-pyrrolo[3,4-b]pyridin-6-yl]-2-(4-fluorophenyl)-8-methyl-3-(1h-pyrrolo[2,3-b]pyridin-4-yl)imidazo[1,2-b]pyridazine Chemical compound C([C@H]1CCCN([C@H]1C1)C)N1C(=NN1C=2C=3C=4C=CNC=4N=CC=3)C=C(C)C1=NC=2C1=CC=C(F)C=C1 XWNMOLQVBLTAJA-XXBNENTESA-N 0.000 claims 1
- XWNMOLQVBLTAJA-WMZHIEFXSA-N 6-[(4as,7as)-1-methyl-3,4,4a,5,7,7a-hexahydro-2h-pyrrolo[3,4-b]pyridin-6-yl]-2-(4-fluorophenyl)-8-methyl-3-(1h-pyrrolo[2,3-b]pyridin-4-yl)imidazo[1,2-b]pyridazine Chemical compound C([C@@H]1CCCN([C@@H]1C1)C)N1C(=NN1C=2C=3C=4C=CNC=4N=CC=3)C=C(C)C1=NC=2C1=CC=C(F)C=C1 XWNMOLQVBLTAJA-WMZHIEFXSA-N 0.000 claims 1
- SBADSPUATYWPEN-UHFFFAOYSA-N 9-[2-(4-fluorophenyl)-3-(1h-pyrrolo[2,3-b]pyridin-4-yl)imidazo[1,2-b]pyridazin-6-yl]-2,9-diazaspiro[5.5]undecane Chemical compound C1=CC(F)=CC=C1C1=C(C=2C=3C=CNC=3N=CC=2)N2N=C(N3CCC4(CNCCC4)CC3)C=CC2=N1 SBADSPUATYWPEN-UHFFFAOYSA-N 0.000 claims 1
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- 208000017164 Chronobiology disease Diseases 0.000 claims 1
- 206010012335 Dependence Diseases 0.000 claims 1
- 208000020401 Depressive disease Diseases 0.000 claims 1
- 208000019022 Mood disease Diseases 0.000 claims 1
- RPBVRTUEQYPDOK-UHFFFAOYSA-N [4-[2-(4-fluorophenyl)-3-(1h-pyrrolo[2,3-b]pyridin-4-yl)imidazo[1,2-b]pyridazin-6-yl]piperazin-2-yl]methanol Chemical compound C1CNC(CO)CN1C1=NN2C(C=3C=4C=CNC=4N=CC=3)=C(C=3C=CC(F)=CC=3)N=C2C=C1 RPBVRTUEQYPDOK-UHFFFAOYSA-N 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 230000036506 anxiety Effects 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 239000012752 auxiliary agent Substances 0.000 claims 1
- 230000004663 cell proliferation Effects 0.000 claims 1
- 238000010511 deprotection reaction Methods 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 230000006951 hyperphosphorylation Effects 0.000 claims 1
- OXSABAZYSCHBEW-UHFFFAOYSA-N imidazo[1,2-b]pyridazine Chemical compound N1=C=CC=C2N=C[CH]N21 OXSABAZYSCHBEW-UHFFFAOYSA-N 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 208000019116 sleep disease Diseases 0.000 claims 1
- 201000009032 substance abuse Diseases 0.000 claims 1
- 231100000736 substance abuse Toxicity 0.000 claims 1
- 208000011117 substance-related disease Diseases 0.000 claims 1
- 102000013498 tau Proteins Human genes 0.000 claims 1
- 108010026424 tau Proteins Proteins 0.000 claims 1
- 125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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- A61P9/06—Antiarrhythmics
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- A—HUMAN NECESSITIES
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- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
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- Heart & Thoracic Surgery (AREA)
- Anesthesiology (AREA)
- Oncology (AREA)
- Urology & Nephrology (AREA)
- Hematology (AREA)
- Hospice & Palliative Care (AREA)
- Vascular Medicine (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0806723A FR2939134A1 (fr) | 2008-12-01 | 2008-12-01 | Derives de 6-cycloamino-3-(1h-pyrrolo°2,3-b!pyridin-4-yl) imidazo°1,2-b!-pyridazine, leur preparation et leur application en therapeutique |
| EP09797121.2A EP2370446B1 (de) | 2008-12-01 | 2009-11-30 | 6-cycloamino-3-(1h-pyrrolo[2,3-b]pyridin-4-yl)imidazo[1,2-b]pyridazinderivate, deren herstellung und deren therapeutische verwendung |
| PCT/FR2009/052336 WO2010063929A1 (fr) | 2008-12-01 | 2009-11-30 | DERIVES DE 6-CYCLOAMINO-3-(1H-PYRROLO[2,3-b]PYRIDIN-4-YL)IMIDAZO[1,2-b]-PYRIDAZINE, LEUR PREPARATION ET LEUR APPLICATION EN THERAPEUTIQUE |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20160173T1 true HRP20160173T1 (hr) | 2016-03-25 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20160173T HRP20160173T1 (hr) | 2008-12-01 | 2016-02-16 | Derivati 6-cikloamino-3-(1h-pirolo[2,3-b]piridin-4-il)imidazo[1,2-b]piridazina, njihova priprema i njihova terapijska primjena |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US8546395B2 (de) |
| EP (1) | EP2370446B1 (de) |
| JP (1) | JP5677309B2 (de) |
| KR (1) | KR20110082094A (de) |
| CN (1) | CN102232079A (de) |
| AR (1) | AR074237A1 (de) |
| AU (1) | AU2009323968A1 (de) |
| BR (1) | BRPI0922760A2 (de) |
| CA (1) | CA2743560A1 (de) |
| CY (1) | CY1117529T1 (de) |
| DK (1) | DK2370446T3 (de) |
| ES (1) | ES2563085T3 (de) |
| FR (1) | FR2939134A1 (de) |
| HR (1) | HRP20160173T1 (de) |
| HU (1) | HUE028525T2 (de) |
| IL (1) | IL213208A0 (de) |
| MX (1) | MX2011005808A (de) |
| PA (1) | PA8849801A1 (de) |
| PL (1) | PL2370446T3 (de) |
| PT (1) | PT2370446E (de) |
| RS (1) | RS54656B1 (de) |
| RU (1) | RU2011126981A (de) |
| SG (1) | SG172757A1 (de) |
| SI (1) | SI2370446T1 (de) |
| TW (1) | TW201033209A (de) |
| UY (1) | UY32280A (de) |
| WO (1) | WO2010063929A1 (de) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UA100684C2 (uk) * | 2007-03-15 | 2013-01-25 | Новартіс Аг | Похідні бензилу та піридинілу як модулятори сигнального шляху hedgehog |
| US20100041663A1 (en) * | 2008-07-18 | 2010-02-18 | Novartis Ag | Organic Compounds as Smo Inhibitors |
| JP5944497B2 (ja) * | 2011-06-22 | 2016-07-05 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ | ヘテロシクリルアミノイミダゾピリダジン |
| US20230192699A1 (en) * | 2020-03-27 | 2023-06-22 | Gritscience Biopharmaceuticals Co., Ltd. | Compounds as casein kinase inhibitors |
| IL312114A (en) | 2021-10-14 | 2024-06-01 | Incyte Corp | Quinoline compounds as Kras inhibitors |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100439367C (zh) | 2003-12-11 | 2008-12-03 | 安万特药物公司 | 作为酪蛋白激酶Iε抑制剂的取代的1H-吡咯并[3,2-b、3,2-c和2,3-c]吡啶-2-甲酰胺以及相关类似物 |
| US7750000B2 (en) * | 2005-09-02 | 2010-07-06 | Bayer Schering Pharma Ag | Substituted imidazo[1,2b]pyridazines as kinase inhibitors, their preparation and use as medicaments |
| DE102005042742A1 (de) * | 2005-09-02 | 2007-03-08 | Schering Ag | Substituierte Imidazo[1,2b]pyridazine als Kinase-Inhibitoren, deren Herstellung und Verwendung als Arzneimittel |
| AR064420A1 (es) * | 2006-12-21 | 2009-04-01 | Alcon Mfg Ltd | Composiciones farmaceuticas oftalmicas que comprenden una cantidad efectiva de analogos de 6-aminoimidazo[1,2b]piridazinas, utiles para el tratamiento del glaucoma y/o controlar la presion intraocular normal o elevada(iop). |
| JP2010526120A (ja) * | 2007-05-09 | 2010-07-29 | ノバルティス アーゲー | Ｐｉ３ｋ脂質キナーゼ阻害剤としての置換イミダゾピリダジン |
| PE20090288A1 (es) * | 2007-05-10 | 2009-04-03 | Smithkline Beecham Corp | Derivados de quinoxalina como inhibidores de la pi3 quinasa |
| AR067326A1 (es) * | 2007-05-11 | 2009-10-07 | Novartis Ag | Imidazopiridinas y pirrolo -pirimidinas sustituidas como inhibidores de cinasa de lipido |
| FR2918061B1 (fr) * | 2007-06-28 | 2010-10-22 | Sanofi Aventis | Derives de 6-cycloamino-3-(pyridin-4-yl)imidazo°1,2-b!- pyridazine,leur preparation et leur application en therapeutique. |
| FR2918986B1 (fr) * | 2007-07-19 | 2009-09-04 | Sanofi Aventis Sa | Derives de 6-cycloamino-3-(pyridazin-4-yl)imidazo[1,2-b]- pyridazine, leur preparation et leur application en therapeutique |
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2008
- 2008-12-01 FR FR0806723A patent/FR2939134A1/fr active Pending
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2009
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- 2009-11-30 MX MX2011005808A patent/MX2011005808A/es not_active Application Discontinuation
- 2009-11-30 PT PT97971212T patent/PT2370446E/pt unknown
- 2009-11-30 CA CA2743560A patent/CA2743560A1/fr not_active Abandoned
- 2009-11-30 PL PL09797121T patent/PL2370446T3/pl unknown
- 2009-11-30 SG SG2011038361A patent/SG172757A1/en unknown
- 2009-11-30 AR ARP090104598A patent/AR074237A1/es unknown
- 2009-11-30 TW TW098140839A patent/TW201033209A/zh unknown
- 2009-11-30 DK DK09797121.2T patent/DK2370446T3/en active
- 2009-11-30 SI SI200931370T patent/SI2370446T1/sl unknown
- 2009-11-30 BR BRPI0922760-1A patent/BRPI0922760A2/pt not_active IP Right Cessation
- 2009-11-30 WO PCT/FR2009/052336 patent/WO2010063929A1/fr active Application Filing
- 2009-11-30 HU HUE09797121A patent/HUE028525T2/hu unknown
- 2009-11-30 EP EP09797121.2A patent/EP2370446B1/de active Active
- 2009-11-30 AU AU2009323968A patent/AU2009323968A1/en not_active Abandoned
- 2009-11-30 KR KR1020117015085A patent/KR20110082094A/ko not_active Application Discontinuation
- 2009-11-30 CN CN2009801481699A patent/CN102232079A/zh active Pending
- 2009-11-30 RS RS20160093A patent/RS54656B1/en unknown
- 2009-11-30 RU RU2011126981/04A patent/RU2011126981A/ru unknown
- 2009-11-30 JP JP2011538042A patent/JP5677309B2/ja not_active Expired - Fee Related
- 2009-11-30 ES ES09797121.2T patent/ES2563085T3/es active Active
- 2009-12-01 UY UY0001032280A patent/UY32280A/es not_active Application Discontinuation
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2011
- 2011-05-29 IL IL213208A patent/IL213208A0/en unknown
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2016
- 2016-02-16 HR HRP20160173T patent/HRP20160173T1/hr unknown
- 2016-02-24 CY CY20161100152T patent/CY1117529T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK2370446T3 (en) | 2016-02-22 |
| WO2010063929A1 (fr) | 2010-06-10 |
| PA8849801A1 (es) | 2010-07-27 |
| PT2370446E (pt) | 2016-03-22 |
| EP2370446B1 (de) | 2015-11-25 |
| JP5677309B2 (ja) | 2015-02-25 |
| AR074237A1 (es) | 2010-12-29 |
| AU2009323968A1 (en) | 2010-06-10 |
| TW201033209A (en) | 2010-09-16 |
| ES2563085T3 (es) | 2016-03-10 |
| RU2011126981A (ru) | 2013-01-10 |
| SI2370446T1 (sl) | 2016-03-31 |
| EP2370446A1 (de) | 2011-10-05 |
| US20120010208A1 (en) | 2012-01-12 |
| BRPI0922760A2 (pt) | 2018-11-06 |
| IL213208A0 (en) | 2011-07-31 |
| UY32280A (es) | 2010-06-30 |
| CA2743560A1 (fr) | 2010-06-10 |
| HUE028525T2 (hu) | 2016-12-28 |
| US8546395B2 (en) | 2013-10-01 |
| CN102232079A (zh) | 2011-11-02 |
| FR2939134A1 (fr) | 2010-06-04 |
| RS54656B1 (en) | 2016-08-31 |
| MX2011005808A (es) | 2011-10-11 |
| SG172757A1 (en) | 2011-08-29 |
| KR20110082094A (ko) | 2011-07-15 |
| JP2012510453A (ja) | 2012-05-10 |
| CY1117529T1 (el) | 2017-04-26 |
| PL2370446T3 (pl) | 2016-05-31 |
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